Boron tribromide → HCID 15765397, compound

HRID 2225429Notes

Reaction equation

HRID 2225429 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[C:3]1=[O:21].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C:3]1=[O:21]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18981050HCID 18981050, compound

Product 1

HCID 15765397HCID 15765397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a flask were placed 25.88 g (0.086 mole) of 1-methyl-3-(4-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione and 200 mL of methylene chloride. To this flask was added dropwise 258 mL (0.258 mole) of a 1 molar solution of boron tribromide in methylene chloride. Upon completion of addition, this reaction mixture was allowed to stir at ambient temperature for approximately 64 hours after which it was poured over ice. This mixture was filtered to remove insoluble material, and the aqueous and organic layers of the filtrate were separated. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure, leaving 1-methyl-3-(4-hydroxyphenyl)-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione as a residue. The NMR spectrum was consistent with proposed structure.

Workup

  1. customIn a flask were placed
  2. additionUpon completion of addition
  3. additionwas poured over ice
  4. filtrationThis mixture was filtered
  5. customto remove insoluble material
  6. customthe aqueous and organic layers of the filtrate were separated
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6aa6bbc5cab948929afe12faff01ad45
Source dataset
uspto-grants-1994_09
Patent number
US05344812

Reaction notes

Loading…